Biopolym. Cell. 1993; 9(3):17-22.
Structure and Function of Biopolymers
The investigation of interactions of hypoxanthine, xanthine and their methyl and glycosyl derivatives with amino acid carboxylic group by spectroscopic methods
- Institute of Molecular Biology and Genetics, NAS of Ukraine
150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680
Abstract
The interactions of some methyl and glycosyl derivatives of hypo-xanthine and xanthine with ionized and neutral amino acid carboxylic group were investigated in dimethylsulfoxide. It was established that ionized carboxylic group forms complexes with hypoxanthine, inosine, xanthine, 3-methylxanthine and 9-methylxanthine. In the last case the proton transfer occurs from the base to carboxylate-ion. The methylation of hypoxanthine and xanthine nucleosides at N7 atoms results in their ability to interact with a neutral carboxylic group. The weak interaction with neutral carboxylic group was observed in the case of 9,-methylxanthine. 1-Methylxanthine proved to be indifferent to the two forms of carboxylic group.
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References
[1]
Zheltovsky NV, Samoilenko SA, Kolomiets IN, Kondratyuk IV, Gubaidullin MI. Some structural aspects of protein-nucleic acid recognition point mechanisms involving amino acid carboxylic groups. J Mol Struct. 1989;214:15–26.
[2]
Lancelot G, Hélène C. Selective recognition of nucleic acids by proteins: the specificity of guanine interaction with carboxylate ions. Proc Natl Acad Sci U S A. 1977;74(11):4872-5.
[3]
Bruskov VI, Bushuev VN. Study by the proton magnetic resonance method of complex formation between nucleosides and compounds modeling amino acid residues of proteins in dimethyl sulfoxide. Biofizika. 1977;22(1):26-31.
[4]
Zheltovskiy NV, Samoylenko SA, Kolomiets IN, Kondratiuk IV. Interaction of nucleobases with the amino acids carboxyl grouP in DMSO: a model of Point Protein-nucleic contacts. Doklady Akad Nauk Ukr SSR. Ser B. 1988; (8):68-71.
[5]
Kondratyuk IV, Kolomiets IN, Samoilenko SA, Zheltovsky NV. A study of complexes between cytosine bases and amino acid carboxylic group by NMR spectroscopy. Biopolym Cell. 1989; 5(6):21-5.
[6]
Kolomiets IN, Kondratyuk IV, Stepanyugin AV, Samoilenko SA, Zheltovsky NV. Influence of methylation of nucleic acid purine bases on their interactions with amino acids through the carboxylic group. J Mol Struct 1991;250(1):1–11.
[7]
Gul'tiaev AP, SamoÄlenko SA, ZheltovskiÄ NV. Spectroscopic study of interactions between nucleic acid bases and amino acid esters in dimethylsulfoxide. Mol Biol (Mosk). 1981;15(6):1295-302.
[8]
Tsuboi M, Takahashi S. Infrared and Raman spectra of nucleic acids. Vibrations in the base-residues. Physico-chemical properties of nucleic acids.— New York: Acad, press. 1973; Pt. 2:91-145.
[9]
Breiimaier E, Voelter W. Carbon-13 NMR spectroscopy. Weinheim: VCH, 1987. 515 p.
[10]
Jones AJ, Grant DM, Winkley MW, Robins RK. Carbon-13 magnetic resonance. XVII. Pyrimidine and purine nucleosides. J Am Chem Soc. 1970;92(13):4079–87.
[11]
Lichtenberg D, Bergmann F, Neiman Z. Tautomeric forms and ionisation processes in xanthine and its N-methyl derivatives. J Chem Soc. 1971;1676-82.